380632-68-8

Basic information

• Product Name: 2,4(1H,3H)-Quinolinedione, 3-chloro-3-methyl-1-phenyl-
• Synonyms: 3-chloro-3-methyl-1-phenyl-2,4(1H,3H)-quinolinedione
• CAS NO: 380632-68-8
• Molecular Formula: C₁₆H₁₂ClNO₂
• Molecular Weight: 285.72498
• Mol File: 380632-68-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,4(1H,3H)-Quinolinedione, 3-chloro-3-methyl-1-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4(1H,3H)-Quinolinedione, 3-chloro-3-methyl-1-phenyl-(380632-68-8)
• EPA Substance Registry System: 2,4(1H,3H)-Quinolinedione, 3-chloro-3-methyl-1-phenyl-(380632-68-8)

Safety Data

• Hazardous Substances Data: 380632-68-8(Hazardous Substances Data)

Upstream product

• 94298-58-5 4-hydroxy-1-phenyl-3-methyl-1H-quinolin-2-one 

Downstream Products

• 477950-16-6 3-butylamino-3-methyl-1-phenylquinoline-2,4(1H,3H)-dione 
• 477950-14-4 3-amino-3-methyl-1-phenylquinoline-2,4(1H,3H)-dione 
• 94298-58-5 4-hydroxy-1-phenyl-3-methyl-1H-quinolin-2-one 
• 369651-50-3 3-hydroxy-3-methyl-1-phenyl-2,4(1H,3H)-quinolinedione 

Relevant articles and documents

Reaction of some 2-quinolone derivatives with phosphoryl chloride: Synthesis of novel phosphoric acid esters of 4-hydroxy-2-quinolone

3-Chloroquinoline-2,4-diones do not react with phosphoryl chloride, however, 2,4-dichloroquinolines and/or 4-chloroquinolin-2-ones are formed in the presence of N,N-dimethylaniline. Along with these compounds, small quantities of novel dihydrogen phosphates of 4-hydroxyquinolin-2-ones were isolated. We outline a simple procedure that allows for the preparation of these compounds in moderate to good yields. All compounds were characterized by 1H and 13C NMR, IR, EI-MS, and ESI-MS spectroscopy, and in select cases by 31P NMR spectroscopy.

Syntheses of 3-aminoquinoline-2,4(1H,3H)-diones

Reaction of 3-chloro- (2) and 3-bromoquinoline-2,4(1H,3H)-diones (3) with excess of primary alkyl- or arylamines in dimethylformamide provides the corresponding 3-alkyl- or 3-arylamino derivatives (4). Compounds (4) with the primary amino group at the 3 position were best prepared by reaction of 2 with in situ generated ammonia under anhydrous conditions. An alternative approach to the primary amines (4) via reduction of 3-azidoquinoline-2,4(1H,3H)-diones (5) was investigated. The reduction of 5 with zinc in acetic acid gave moderate to good yields of the desired products, while the reaction with triphenylphosphine afforded exclusively 4-hydroxyquinolin-2(1H)-one (1).